The formation and fragmentation of flavonoid radical anions

Linda Feketeová, Christopher K. Barlow, Timothy M. Benton, Simone J. Rochfort, Richard Alfred John O'Hair

Research output: Contribution to journalArticleResearchpeer-review

13 Citations (Scopus)

Abstract

Negative electrospray ionization of iron(III) salen complex of flavonoids, M, was used in conjunction with collision-induced dissociation (CID) to examine the formation and subsequent fragmentation reactions of their radical anions [M-2H]•- Sixteen different flavonoids were investigated from three different sub-groups (flavanone, flavone and flavanol). All formed the desired iron salen complex, [FeIII(salen)(M-2H)]-•, and all but one of these complexes produced the radical anion upon CID. The CID fragmentation reactions of these radical anions, [M-2H]-•, were compared to their even electron counterparts [M-H]-•. Generally the former provided more structural information, with novel cross-ring cleavages of sugar(s) often being observed. Isomeric flavonoids can often be distinguished based on the differences in the fragmentation pathways of their radical anions. Crown

Original languageEnglish
Pages (from-to)174-183
Number of pages10
JournalInternational Journal of Mass Spectrometry
Volume301
Issue number1-3
DOIs
Publication statusPublished - 30 Mar 2011
Externally publishedYes

Keywords

  • Collision-induced dissociation
  • Electrospray ionization
  • Flavonoid
  • Metal complex
  • Radical anion

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